John Herrington was driving his car across San Francisco’s Bay Bridge, on his way to an amateur boxing match in 1978, when he first heard of James Webb. The young author was on the radio to promote Fields of Fire, his just-published novel about the Vietnam War. Herrington might not have remembered the broadcast, if it hadn’t been for an exchange in its final moments. The host of the show mentioned that a certain actress was coming to town. There was a long pause. “Jane Fonda can kiss my a**,” said Webb. “I wouldn’t go across the street to watch her slit her wrist.”

Herrington has told this story before — it appears in The Nightingale’s Song, by Robert Timberg — and he enjoys telling it now, after almost three decades. “Words like that really grab your attention,” he says. Herrington eventually helped Webb secure his first job in the Reagan administration, as an assistant secretary of defense. Now Webb is trying to use this experience to get elected to the Senate — as an anti-war Democrat from Virginia. “If [Reagan] was alive today, I think he’d be a Democrat again,” said Webb in July. Amazingly, this Fonda-hater is now on the verge of upsetting Republican senator George Allen, a favorite of many conservatives and a first-tier candidate for the GOP presidential nomination in 2008. Several recent polls show Webb trailing Allen by only a few points, in what has become perhaps the nastiest race in the country.

One thing’s sure about Webb: He doesn’t mince words. In fact, he deploys them to great effect. “He’s a poet,” says Herrington, who has read each of Webb’s six novels. Twenty years ago, Tom Wolfe called him “one of the four or five most important young writers in this country.” Years from now, no matter what happens on November 7, people will still read Webb’s books and possibly regard him as a top-ranking war novelist, in the vein of Stephen Crane, Erich Maria Remarque, and Nicholas Monsarrat.

Before Webb was a writer he was a war hero. He graduated from Annapolis and went to Vietnam. As a Marine lieutenant in 1969, he used his body to shield a corporal from an exploding grenade. For this and other acts of bravery, he earned the Navy Cross — on the valor scale, that’s just a notch below the Medal of Honor. There’s still a piece of shrapnel stuck in his head. He went on to earn a law degree from Georgetown, began writing books, and served in the Reagan administration, where he eventually rose to secretary of the Navy.

Webb is now 60, and he’s certainly no ordinary Democrat. He grew up in the party of FDR, but the liberalism of the 1970s drove him out. “Jimmy Carter made me a Republican,” he said in 1985. Bill Clinton kept him one — or at least kept him away from his political roots: “I cannot conjure up an ounce of respect for Bill Clinton when it comes to the military,” Webb said in 1997. “Every time I see him salute a Marine, it infuriates me. I don’t think Bill Clinton cares one iota about what happens in a military unit.” In 2000, at an event to endorse Allen in his race against Democratic senator Chuck Robb, Webb again opened fire on Clinton: “We are now coming off a period of eight years of the most corrupt administration in modern memory.”

This newly minted Democrat doesn’t have a very high opinion of John Kerry, either. For years, he refused to shake Kerry’s hand on account of his anti-war activism. As Kerry ran for president in 2004, Webb insisted that the Massachusetts senator continued to owe Vietnam-era veterans “a full and complete apology” because he “defamed a generation of honorable men.” Later, in the heat of the campaign, he said that Kerry had “earned the karma” that the Swift Boat veterans visited upon him in their negative ads.

But Webb also says he voted for Kerry because he disagreed so thoroughly with President Bush’s policy on Iraq. Webb was in fact an early critic of the war: Writing in the Washington Post in 2002, more than six months before the first bombs fell on Baghdad, he warned that “there is no exit strategy if we invade and stay” and that American soldiers in an occupation force “would quickly become 50,000 terrorist targets.” But if he seems like a Cassandra today, he was less of one in 1990, when he questioned military action following Saddam Hussein’s invasion of Kuwait: “Those who believe we should use [U.S. troops] offensively should realize that this would galvanize the Arab world, invite chemical retaliation and an expansion of the hostilities, produce great numbers of casualties, and encourage worldwide terrorism — in short, open up a Pandora’s box.” This prediction didn’t exactly come true, even as the war solved some problems and created new ones.

Webb once excoriated the Clinton administration for having “a national-security team [that] is composed of people who have never worn a uniform.” This is by no means an invalid observation: Military experience is an important asset for political leaders to possess, and today there are fewer and fewer veterans in Washington’s halls of power. Yet when Webb raises this point in the context of a specific policy disagreement, he often sinks to ad hominem name-calling. During a debate with Allen on September 17, as the candidates argued about Iraq, Webb quoted something his son recently told him: “Dad, you were — you fought in Vietnam. George Allen didn’t fight in Vietnam. Even the French fought in Vietnam!” A few minutes later, Webb described the architects of Hussein’s ouster as “theorists who have never been on a battlefield, who have never put a uniform on.” As if any of this were relevant. (Last year, incidentally, a Pew Research Center poll found that 64 percent of male veterans believed that U.S. troops should remain in Iraq until it’s stabilized, compared to 55 percent of non-veteran men.)

Conservatives have long admired Webb for his tough talk. In 2000, he likened affirmative action to “state-sponsored racism that is as odious as the Jim Crow laws it sought to countermand” — blistering words, even for a critic of the practice. He added that these policies are enforced by “a Soviet-style bureaucracy of political commissars.” In the 1970s, he criticized the sexual integration of the U.S. Naval Academy: “I have never met a woman . . . whom I would trust to provide [soldiers] with combat leadership.” He also stood up for the Navy during the Tailhook scandal, lamenting that the “inexcusable harassment of women” had transformed into a reckless “witch hunt” that destroyed upright careers. This has prompted Allen to launch ham-handed, quasi-feminist attacks on Webb that are meant to influence female voters. These may backfire, reminding conservatives that Webb is unafraid to buck political correctness.

Except that this is no longer as true as it once was. Webb has retreated from his principled opposition to affirmative action, now saying that racial preferences should be either limited to native-born blacks or else expanded to include poor whites. This isn’t exactly in line with liberal dogma, but it signifies a clear departure from his previous view. What’s more, Webb’s most recent book, a nonfiction history of Scots-Irish culture, contains a heartfelt passage that condemns the “Nazification of the Confederacy” — i.e., allowing “revisionist politicians and academics” to demonize every aspect of southern history. Yet Webb has watched silently as his surrogates have tried to paint Allen as a racist for owning a collection of Confederate flags and wearing a stars-and-bars lapel pin in a high-school yearbook photo. By the end of September, the two campaigns were involved in a tedious shouting match over which candidate had uttered fewer racial epithets.

If this mad dash to seize the low ground has been a disappointment to the normally cerebral Webb, he hasn’t said so. Perhaps that’s because these distractions have called attention away from all of the liberal positions he has publicly adopted since becoming a Democratic candidate: He’s pro-choice on abortion, supports civil unions for gays, wants to repeal the Bush tax cuts, bashes Wal-Mart, and has said he would have voted against confirming Samuel Alito to the Supreme Court. Former Democratic senator John Edwards, who stumped for Webb on September 26, likes to give a class-warfare speech about the haves and have-nots who live in “two Americas.” Webb does him one better, with his references to “three Americas” — the carefree rich, the outsourced middle, and the wage-slave poor. At times, Webb has sounded patently ridiculous: “We are in danger of developing a permanent underclass, without true hope of advancement,” he said in an interview on the Daily Kos website. “We are starting to look a bit like Manila — walled communities, different schools for the elites, and people living out of boxes.”

Still, in the space of several months, Webb has gone from being an untested candidate facing long odds against a GOP Goliath to a slight underdog in a tight race against a roughed-up opponent. Allen may yet recover from his gaffes and strategic blunders, spend like crazy, and eke out a narrow victory. But whatever happens, the race is bound to have repercussions beyond this fall: If Webb prevails, he may provide Democrats with the surprise win they need in order to gain control of the Senate. If he loses, he may well run again in the near future — especially if the situation in Iraq remains dicey and Virginia’s other Republican senator, the 79-year-old John Warner, doesn’t seek reelection. More immediately, however, he will have done Democrats a huge favor by turning a red-state contest into a close call and delivering a hard blow to Allen’s prospects in 2008. At a minimum, Webb may have the makings of a novel about how politics is war by other means.